Azo dyestuff containing a chrysene nucleus



" 7 The following example serves to illustrate'the of example o-hydroxy carboxylic acid arylamacid, 2-hydroxy-a-benzocarbazole 3 carboxylic Our new dyestuffs are obtainablebyidiazotizno) -3-nitrobenzene of the formula.

3340 the known methods of producing ice colors generally yield blue to violet to brown shades of good I 1 der Deutschen Chemischen Gesellschaft, Vol.23, the dyestufi from diazochrysene and 1(2',3'-hy- Patented Dec. 18, 1934 1,984,722

AZO DYESTUFF CONTAINING A CHRYSENE' NUCLEUS Alfred Bergdolt, Cologne-on-the-Rhine, and

Albert Schmelzer, Cologne-Mulheim-on-the- Rhine, Germany, assignors to General Aniline Works, Inc., New York N, I, a corporation of Delaware q No Drawing. Application December 6, 1932, Serial No. 646,024. In Germany December 18, 1931 x 12 Claims. (Cl. 260-86) The present invention relates to new water in- 1890, page 244 sequ. From our present knowledge 2' soluble azo dyestuffs, more particularly it re- We cannot definitely state at what position the hates to azo dyestuffs which may be'represented nitro group enters the chrysene, and therefore the by the probable general formula constitution of the amino chrysene used is not r known. 5

, invention, without limiting it thereto:- 1 ExampZe -H-BO parts by weight of cotton yarn I are treated in the usual manner with a' solution containing in one litre 6 partsby weight of 2- hydroxy-naphthoylaminobenzene for half an hour r at 30 C. The yarn is well squeezed and introduced for about half an hour into a diazo solution prepared in the usual manner from 2.45 parts t by weight of amino-chrysene which bath has 15 been neutralized by sodium bicarbonate and to which 20 parts by Weight of zinc sulfate have .been added. The yarn is then rinsed, soaped while boiling and dried. A bluish violet of excellent fastness to boiling and chlorine is thus 20 obtained.

The dyestuff has the following formula:

wherein n stands for one of the numbers one and two, R stands for theradical of a coupling component suitable for producing an azodyestufl .iree from agroup inducing solubility in water, such as a sulfonic' 'or carboxylic acid group; that means'in the coupling component suitable for producing our new azo dyestufis, therelmay be present substituents such as alkyl,. alkoxy, halogen, the nitro group, a substituted amino group etc. As coupling components preferably used in our invention there may be mentioned'by way 25 ides of naphthalene or arylamides of hydroxy carboxylicxacidsof other aromatic ring systems, such as arylamides of 2-hydroxy-3-anthracene carboxylic acid, 2 hydroxy-carbazole 3-carboxylic 3o acid (see U. S.-Patent '1,867,l06)' and the like,

aceto-acetic acid arylamides and derivatives thereof, such as bis-(aceto-acetic acid arylam-. in an analogous manner thedyestufi from diaides). zochrysene and 1-(2,3-hydroxynaphthoylamiing'in the usualmanner aminochrysene and coupling in substance or on the fibre with a coupling NO.

component of the kind referred to above. The dyestufis when produced on the fibre according to OH OCFNHO fastness to boiling and chlorine.

The amino-ehrysene used as diazotization component in our invention is obtainable by nitrating chrysene occurring in the high boiling fractions of coal tar and reducing the nitro compound .to form the corresponding amino comv pound a rd to the direfition given in e e yields a navy blue of similar fastnessproperties;

droxynaphthoylamino)-naphthalene of the formula yields a reddish navy blue of the same fastness properties; the dyestuff from diazochrysene and 1 (5 hydroxy 1,2,l,2 benzocarbazole 4' carbonylamino) 2 methyl 4 methoxybenzene of the formula yields a dark blue of similar fastness properties; the dyestufi from diazochrysene and 4,4'-acetoacetylamino-3,3'-dimethyl-diphenyl of the formula yields a yellowish brown of good fastness properties. The dyestuff from diazochrysene and acetoacetic acid anilide of the formula yields a yellowish-brown of good 'fastness properties.

We claim:

1. Water insoluble dyestuffs of the general formula wherein n stands for one of the numbers one and two and R stands for the radical of a coupling component suitable for producing an azo dyestuff free from a group inducing solubility in Water,

yielding when produced on the fibre generally blue to violet to brown shades of good fastness to boiling and chlorine.

2. Water insoluble dyestuffs of the formula wherein R stands for the radical of a coupling component suitable for producing an azo dyestuif free from a group inducing solubility in water, yielding when produced on the fibre generally blue to violet to brown shades of good fastness to boiling andchlorine.

mula

wherein R stands for a radical of the naphthalene .i or benzocarbazole series, R stands for a radical 3. Water insoluble dyestuffs of the general forof the benzene or'naphthalene series, the OH group stands in ortho position to the group CONH-R and wherein Rand R may be substituted by substituents selected frointhe group yielding when produced on the fibre a bluish violet of excellent fastness to boiling and chlorine.

'5. The dyestufi of the following formula yielding when produced on the fibre a reddish navy blue of excellent fastness to boili chlorine.

ng and 6. The dyestufi of the following formula:

5 amo yielding when produced on the fibre adark blue 10. Fibres dyed with a dyestufi as claimed in of excellent fastness to boiling and chlorine. claim 4.

7. Fibres dyed with a dyestufi as claimed in 11. Fibres dyed with a dyestuif as claimed in 15 claim 1'. claim 5.

8. Fibres dyed with a dyestufi as claimed in 12. Fibres dyed with a dyestufi as claimed in claim 2. 7 claim 6.

9. Fibres dyed with a dyestufi as claimed in claim 3.

ALFRED BERGDOLT. ALBERT SCHMELZER. 

